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Weekend Delivery Independent Contractor Jobs in Chicago, IL

MCSW Capital Enterprises LLC

Contractor

Chicago, IL · On-site

Contract/Independent Contractor position * On-site route-based work * Car, SUV, or minivan required * Scheduled courier deliveries and pickups * Must be dependable, punctual, and able to follow ...

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All JobsDelivery Independent Contractor JobsWeekend Delivery Independent Contractor JobsWeekend Delivery Independent Contractor Jobs in Chicago, IL

Weekend Delivery Independent Contractor information

See Chicago, IL salary details

$13

$47

$94

How much do weekend delivery independent contractor jobs pay per hour?

As of Sep 7, 2026, the average hourly pay for weekend delivery independent contractor in Chicago, IL is $47.75, according to ZipRecruiter salary data. Most workers in this role earn between $21.06 and $62.40 per hour, depending on experience, location, and employer.

What is a weekend delivery independent contractor?

A Weekend Delivery Independent Contractor is a self-employed individual who delivers packages, food, or other goods on weekends for companies or clients. Unlike traditional employees, independent contractors set their own schedules and typically use their own vehicles for deliveries. They are responsible for managing their own taxes, expenses, and insurance. This role is popular with people seeking flexible, part-time work, especially on weekends. Companies often contract with these individuals to meet higher demand during weekends or to provide extended delivery hours.

What are the key skills and qualifications needed to thrive as a weekend delivery independent contractor?

To thrive as a Weekend Delivery Independent Contractor, you typically need a valid driver’s license, a reliable vehicle, and basic knowledge of local routes. Familiarity with GPS navigation apps, delivery tracking platforms, and sometimes background checks or vehicle insurance are also standard requirements. Strong time management, customer service skills, and the ability to work independently help you stand out in this role. These skills ensure timely and accurate deliveries, high customer satisfaction, and efficient problem-solving during weekend shifts.

What are some common challenges faced by weekend delivery independent contractors, and how can they be managed?

Weekend Delivery Independent Contractors often encounter challenges such as unpredictable traffic, last-minute route changes, and managing multiple deliveries within tight timeframes. Effective time management, using reliable navigation apps, and maintaining clear communication with dispatchers or clients can help address these issues. Additionally, being proactive about vehicle maintenance ensures reliability and minimizes disruptions during busy delivery windows. Building familiarity with your delivery area over time will also help streamline routes and improve efficiency.

What is the difference between Weekend Delivery Independent Contractor vs Part-Time Delivery Driver?

AspectWeekend Delivery Independent ContractorPart-Time Delivery Driver
CredentialsNone required, but may need a valid driver’s licenseValid driver’s license, possibly background check
Work EnvironmentFlexible, independent, often self-directedCompany vehicle, scheduled shifts, team environment
Employer UsageTypically contracted through gig platforms or courier companiesEmployed or contracted by delivery companies or restaurants

Weekend Delivery Independent Contractors usually work independently with flexible hours, often through gig platforms, while Part-Time Delivery Drivers are typically employed by companies with scheduled shifts. Both roles involve delivery tasks but differ in work structure and employer relationships.

What are popular job titles related to Weekend Delivery Independent Contractor jobs in Chicago, IL?

For Weekend Delivery Independent Contractor jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Weekend Delivery Independent Contractor jobs in Chicago, IL look for?

The top searched job categories for Weekend Delivery Independent Contractor jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Weekend Delivery Independent Contractor jobs?

Cities near Chicago, IL with the most Weekend Delivery Independent Contractor job openings:

Weekend Delivery Independent Contractor jobs near you
Infographic showing various Weekend Delivery Independent Contractor job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 67% Full Time, 29% Part Time, and 3% Contract. Highlights an 94% Physical, 2% Hybrid, and 4% Remote job distribution, with an average salary of $99,328 per year, or $47.8 per hour.

Commercial Roofing Services - Independent Contractor Companies

City Wide Facility Solutions

Hammond, IN • On-site

Full-time

Re-posted 25 days ago

Key responsibilities

  • Deliver high-quality commercial roofing services, including inspections, leak detection, repairs, and roof replacements.

  • Coordinate with clients and adhere to safety standards while performing work in active commercial environments.

  • Provide proper documentation, reporting, and photo verification of completed work.

Job description

Description
City Wide Facility Solutions is the largest management company in the building maintenance industry. We secure and manage commercial contracts and partner with skilled independent contractors to perform the work. We handle the sales, client communication, billing, and collections - so you can focus on doing what you do best.
We are selectively partnering with established Independent Contractors and service companies to service our commercial clients in the region. If you operate a structured business, deliver professional facility maintenance, restoration, or renovation services, and are looking for steady, recurring work - without the burden of chasing new contracts or managing collections - this may be a strong fit.
City Wide helps you grow your revenue, keep your crews busy, and get paid consistently - including guaranteed payment on the 10th for work performed.
We operate throughout South Chicagoland and Northwest Indiana - a strong commercial market with warehouses, medical facilities, manufacturing sites, schools, and municipal buildings.
For more information, contact Sandra Rivas at 708-365-8535 or chicagoshores-ic@gocitywide.com.
Requirements
We are selectively partnering with contractors who meet the following:
  • Proven experience in commercial roofing (required)
  • Proper licensing for commercial roofing work (as applicable)
  • General liability insurance and workers' compensation coverage
  • Ability to assess, quote, and execute projects independently
  • Professional-grade equipment and crew
  • Strong communication and reliability
  • Commitment to safety, quality, and timelines

Preferred:
  • Experience working in occupied commercial or medical environments
  • Ability to provide clear documentation (photos, reports, scope clarity)

The Opportunity
ity Wide Facility Solutions is seeking a qualified commercial roofing contractor to support a current client project within our portfolio.
This is a project-based opportunity with the potential for ongoing work across multiple commercial properties, depending on performance, professionalism, and execution quality.
We manage a large base of commercial clients across office, medical, industrial, and institutional facilities. Our model is built around bringing vetted service providers into well-scoped, professionally managed opportunities-allowing contractors to focus on execution, not sales.
If you are looking to supplement your pipeline with well-defined commercial work and long-term partnership potential, this may be a strong fit.
If this is your company, keep reading.
INDEPENDENT CONTRACTORS MUST PROVIDE THE FOLLOWING:
  • Valid Business License (if necessary for the service type)
  • Worker's Compensation Insurance
  • General Liability Insurance
  • Federal EIN #
  • Other verifiable business
  • 18 years of age minimum
  • Favorable background investigation results
  • You can not be a sole proprietor

The selected contractor will be responsible for delivering high-quality commercial roofing services, which may include:
  • Roof inspections and condition assessments
  • Leak detection and repair
  • Preventative maintenance
  • Partial or full roof replacement (as applicable)
  • Flat roof systems (TPO, EPDM, modified bitumen, etc.)
  • Proper documentation, reporting, and photo verification

Work will be performed in active commercial environments, requiring professionalism, coordination, and adherence to safety standards.
City Wide will:
  • Coordinate with the client
  • Define scope and expectations
  • Manage communication and administrative flow

You focus on:
Executing the work at a high level
Benefits
We help you grow a real business - not just pick up extra work.
  • Consistent, Recurring Contracts (No Hunting Required)
    We bring you qualified commercial accounts so you can focus on operations - not cold calling, bidding, or chasing leads.
  • Reliable, On-Time Payments
    Eliminate collections headaches. We handle billing and client payment - you get paid consistently and predictably.
  • Scale Your Revenue Quickly
    Access multiple accounts across our territory - grow from a small crew to a multi-team operation with steady work.
  • Professional Account Management Support
    Our Facility Solutions Managers handle client communication, inspections, and issue resolution - helping you retain accounts and maintain high standards.
  • No Sales, No Admin Burden
    We manage contracts, client expectations, and service coordination - freeing you to focus on delivering quality work and building your team.
  • 20+ Other Opportunities
    Expand into additional services (floor care, porter services, consumables, specialty cleaning) and increase revenue per account.
  • Long-Term Partnership Model
    We are invested in your growth - many of our partners have scaled into six-figure and multi-crew businesses with us.

Apply